Pyridylamine compounds are known in the prior art. Indeed, their synthesis schemes can often depend on the nature of the substitutions on various portions of the pyridylamine molecule. Whatever the synthesis route, pyridylamines have been used in a variety of applications. Some examples of their use in catalytic compositions, and methods of forming such catalytic compositions, can be found, e.g., in U.S. Pat. Nos. 6,750,345 and 6,713,577. These patents disclose ligands, complexes, compositions and/or catalysts that provide enhanced olefin polymerization capabilities based on a substituted pyridyl amine structure and hafnium. Other examples of methods of using pyridylamine-containing catalytic compositions for oligomerization reactions can be found, e.g., in U.S. Patent Application Publication Nos. 2007/0185358, 2007/0185360, 2007/0185361, 2007/0185362, and 2007/0185364.
Though some pyridylamines can be manufactured by synthesis routes that are acceptable for bench-scale syntheses, there is a need for alternate synthesis routes that have economic and scale-up advantages for more commercial-scale efforts. The alternate synthesis routes described herein tend to focus on three aspects of improvement: reaction chemistry (e.g., nature of reactants and catalytic/facilitating compounds), temperature control, and number/yield of synthesis steps.